Hydrochloric Acid → HCID 68163114, compound

HRID 924902Notes

Reaction equation

HRID 924902 reaction equation
[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:13][CH2:14][CH2:15][O:16][CH3:17].[C:18]1([C:24](=O)[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH2:33][C:34]([NH2:36])=[O:35].Cl>C(O)C>[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]2[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:36][C:34](=[O:35])[NH:33]2)=[CH:4][C:3]=1[O:13][CH2:14][CH2:15][O:16][CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 86669341HCID 86669341, compound2×

Product 1

HCID 68163114HCID 68163114, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxy-3-(2-methoxyethoxy)-5-nitrobenzaldehyde (Intermediate 80) (200 mg, 0.83 mmol), 1,2-diphenylethanone (196 mg, 1.0 mmol) and urea (150 mg, 2.5 mmol) in ethanol (3 mL) was added conc. HCl (0.2 mL), then the resulting mixture was refluxed for 2 days. The mixture was concentrated under reduced pressure and purified by prep-HPLC (0.1% TFA as additive) to give Compound 155 (162 mg, yield 42%) as yellow solid. 1H NMR (MeOD 400 MHz) δ 7.62 (d, J=1.6 Hz, 1H), 7.27-7.24 (m, 6H), 7.07-7.03 (m, 3H), 6.91-6.86 (m, 2H), 5.37 (s, 1H), 4.17-4.10 (m, 2H), 3.76 (t, J=4.4 Hz, 2H), 3.43 (s, 3H). MS (ESI): m/z 462.1 [M+1]+.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 days
  2. concentrationThe mixture was concentrated under reduced pressure
  3. custompurified by prep-HPLC (0.1% TFA as additive)

Sources & evidence

ORD record
ord-d0ba42219b064547afb8b09dae40f5d8
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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